Barnsley led Manchester United under 21s 2-0 on 82 minutes but lost 3-2 in the EFL Trophy after conceding three times in five minutes.
Vimal Yoganathan’s brace put the home side 2-0 up at half-time but United scored in the 82nd, 84th and 87th minutes.
It was the first of three group games.
Defender Oliver Wilkinson, 15, became the club’s youngest starter, as Darrell Clarke made 11 changes as expected from the league side.
Senior players such as Corey O’Keeffe, Conor McCarthy and Jon Russell started while Kacper Lopata was captain and Josh Benson returned from injury to start.
The Reds did not start any natural strikers with midfielder Yoganathan and wing-back Kyran Lofthouse up front.
Manchester United started England goalkeeper Tom Heaton then a team of youngsters including Jacob Devaney, the son of Barnsley assistant boss Martin Devaney.
Barnsley opened the scoring on 11 minutes when Devaney lost the ball in his penalty area and Lofthouse squared for Yoganathan to finish high into the net from close range.
Ethan Ennis shot across goal and wide from the right of the Barnsley box, after robbing Wilkinson of the ball, then Benson’s header from a right-wing cross was tipped over by Heaton. Benson then shot wide from the edge of the box after a corner was cleared.
Killip made an impressive save with his legs after a good United move saw the home side opened up and Ethan Wheatley went clean through.
Yoganathan scored again with a good finish from seven yards out into the bottom left corner after Lofthouse ran down the left and pulled the ball back form the byline. This time the goal came from a loose Wheatley pass after a United throw-in in their half.
Aiden Marsh, home debutant Josiah Dyer and Harrison Nejman came on at the break for Benson, Russell and Georgie Gent.
Marsh almost scored straight away when United again lost the ball in their box but his shot from a very tight angle on the left trickled across the face of goal.
United nearly pulled one back but Wilkinson and Bland impressively blocked in the box.
Bayley McCann, son of ex-Red Grant, came on for his senior debut.
Ennis pulled one back in the 82nd minute with a smart 15-yard finish after a good move down the right. Jack Fletcher levelled with a stunning 30-yard volley two minutes later.
It was 3-2 on 87 minutes when Fletcher was left unmarked from a throw and finished through Killip.
O’Keeffe was then sent off for an alleged elbow on Harry Amass.
Wheatley could have made it 4-2 after turning Lopata but curled wide deep in the box.
Barnsley (3-5-2): Killip; McCarthy, Lopata, Wilkinson (Barratt 66mins); O’Keeffe, Benson (Nejman HT), Russell (Marsh HT), Bland, Gent (Dyer HT); Yoganathan, Lofthouse (McCann 74).
Unused: Smith, Alker, Barratt.
Goals: Yoganathan 10, 37.
Red cards: O’Keeffe.
Manchester United (4-4-2): Heaton; Ogunneye (Nolan 74mins), Jackson (Aljofree HT), Fredricson, Amass; Devaney, Curley (Fletcher 58), Collier, Mather, Wheatley, Ennis.
Unused: Harrison, Bianchieri, Williams, Sharpe.
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